18471-99-3

Usage

Uses

Used in Pharmaceutical Industry:
1-Methyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid is used as a synthetic intermediate for the development of pharmaceuticals. Its unique structure and potential biological activities contribute to the creation of new drugs with therapeutic benefits.
Used in Antimicrobial Applications:
In the field of microbiology, 1-Methyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid is utilized for its antimicrobial properties. It can be employed as an active ingredient in antimicrobial agents to combat various types of bacteria, thereby contributing to the development of new antibiotics and antimicrobial therapies.
Used in Antiparasitic Applications:
1-Methyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid also has potential applications in antiparasitic treatments. Its ability to target and eliminate parasites makes it a valuable compound in the development of new antiparasitic drugs, addressing the need for novel treatments against various parasitic infections.
Used in Organic Synthesis:
In the realm of organic chemistry, 1-Methyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid serves as a versatile building block for the synthesis of various organic compounds. Its unique structure allows for the formation of diverse chemical entities, expanding the scope of organic synthesis and contributing to the discovery of new chemical compounds with potential applications in various industries.
Used in Medicinal Chemistry:
1-Methyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid is employed in medicinal chemistry for the design and synthesis of new drug candidates. Its potential biological activities and structural features make it a valuable component in the development of innovative therapeutic agents targeting a wide range of diseases and conditions.

InChI:InChI=1/C11H9NO3/c1-12-6-8(11(14)15)10(13)7-4-2-3-5-9(7)12/h2-6H,1H3,(H,14,15)

Upstream product

• 26892-90-0 ethyl 4-hydroxy-3-quinolinecarboxylate 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 
• 860716-87-6 (2-carboxy-1-methyl-4-oxo-1,4-dihydro-[3]quinolyl)-glyoxylic acid 
• 858422-15-8 1,2-dihydroxy-4-methyl-4H-cyclopenta[b]quinoline-3,9-dione 
• 7697-37-2 nitric acid 
• 517-73-7 melicopine 
• 93-61-8 N-methyl-N-phenylformamide 
• 62-53-3 aniline 
• 52980-28-6 ethyl 4-oxo-1,4-dihydroquinoline-3-carboxylate 
• 13721-01-2 4-oxo-1,4-dihydroquinoline-3-carboxylic acid 
• 100-61-8 N-methylaniline 
• 37041-15-9 (N-methyl-anilinomethylene)-malonic acid diethyl ester 
• 23789-85-7 ethyl 1-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylate 

Downstream Products

• 23789-85-7 ethyl 1-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylate 
• 83-54-5 1-methyl-4-quinolone 
• 72361-90-1 1,3-dimethylquinolin-4-one 
• 124502-69-8 N-<4-(4-diphenylmethyl-1-piperazinyl)butyl>-1,4-dihydro-1-methyl-4-oxoquinoline-3-carboxamide 
• 24220-95-9 1-Methyl-3-nitro-4-chinolon 
• 1356829-41-8 C₂₃H₁₆F₃N₃O₂ 
• 1351945-07-7 C₂₄H₁₇F₃N₂O₂ 
• 1356829-35-0 C₂₃H₁₆F₃N₃O₂ 
• 1356829-38-3 C₂₃H₁₆F₃N₃O₂ 
• 1356829-42-9 C₂₃H₁₆F₃N₃O₂ 
• 1356829-44-1 C₂₃H₁₆F₃N₃O₂ 
• 56857-96-6 1-methyl-3-phenylquinolin-4(1H)-one 

Relevant academic research and scientific papers

4-Oxoquinolines and monoamine oxidase: When tautomerism matters

4-Oxoquinoline derivatives have been often used in drug discovery programs due to their pharmacological properties. Inspired on chromone and 4-oxoquinoline chemical structure similarity, a small series of quinoline-based compounds was obtained and screened, for the first time, toward human monoamine oxidases isoforms. The data showed the N-(3,4-dichlorophenyl)-1-methyl-4-oxo-1,4-dihydroquinoline-3-carboxamide 10 was the most potent and selective MAO-B inhibitor (IC50 = 5.30 ± 0.74 nM and SI: ≥1887). The data analysis showed that prototropic tautomerism markedly influences the biological activity. The unequivocal characterisation of the quinoline tautomers was performed to understand the attained data. To our knowledge, there have been no prior reports on the characterisation of quinolone tautomers by 2D NMR techniques, namely by 1H–15N HSQC and 1H–15N HMBC, which are proposed as expedite tools for medicinal chemistry campaigns. Computational studies on enzyme-ligand complexes, obtained after MM-GBSA calculations and molecular dynamics simulations, supported the experimental data.

Structural development of a type-1 ryanodine receptor (RyR1) Ca2+-release channel inhibitor guided by endoplasmic reticulum Ca2+ assay

Type-1 ryanodine receptor (RyR1) is a calcium-release channel localized on sarcoplasmic reticulum (SR) of the skeletal muscle, and mediates muscle contraction by releasing Ca2+ from the SR. Genetic mutations of RyR1 are associated with skeletal muscle diseases such as malignant hyperthermia and central core diseases, in which over-activation of RyR1 causes leakage of Ca2+ from the SR. We recently developed an efficient high-throughput screening system based on the measurement of Ca2+ in endoplasmic reticulum, and used it to identify oxolinic acid (1) as a novel RyR1 channel inhibitor. Here, we designed and synthesized a series of quinolone derivatives based on 1 as a lead compound. Derivatives bearing a long alkyl chain at the nitrogen atom of the quinolone ring and having a suitable substituent at the 7-position of quinolone exhibited potent RyR1 channel-inhibitory activity. Among the synthesized compounds, 14h showed more potent activity than dantrolene, a known RyR1 inhibitor, and exhibited high RyR1 selectivity over RyR2 and RyR3. These compounds may be promising leads for clinically applicable RyR1 channel inhibitors.

Palladium-Nanoparticles-Catalyzed Oxidative Annulation of Benzamides with Alkynes for the Synthesis of Isoquinolones

A novel method to synthesize isoquinolones via oxidative annulation of N-alkoxy benzamides and alkynes using binaphthyl-stabilized palladium nanoparticles (Pd-BNP) as catalyst has been developed. This methodology affords various isoquinolone derivatives in good to excellent yields with high regioselectivities in the presence of air as oxidant. N-Methoxybenzothioamide was also found to undergo oxidative annulation with alkyne successfully and provided a sulfur analogue of isoquinolones in moderate yields. The Pd-BNP catalyst was easily recovered and reused up to four times without any apparent agglomeration. (Figure presented.).

Evaluation of 3-carboxy-4(1H)-quinolones as inhibitors of human protein kinase CK2

Due to the emerging role of protein kinase CK2 as a molecule that participates not only in the development of some cancers but also in viral infections and inflammatory failures, small organic inhibitors of CK2, besides application in scientific research, may have therapeutic significance. In this paper, we present a new class of CK2 inhibitors-3-carboxy-4(1H)-quinolones. This class of inhibitors has been selected via receptor-based virtual screening of the Otava compound library. It was revealed that the most active compounds, 5,6,8-trichloro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (7) (IC 50 = 0.3 μM) and 4-oxo-1,4-dihydrobenzo[h]quinoline-3-carboxylic acid (9) (IC50 = 1 μM), are ATP competitive (Ki values are 0.06 and 0.28 μM, respectively). Evaluation of the inhibitors on seven protein kinases shows considerable selectivity toward CK2. According to theoretical calculations and experimental data, a structural model describing the key features of 3-carboxy-4(1H)-quinolones responsible for tight binding to CK2 active site has been developed.

Pharmacologically active amides and esters containing an azabicycloalkane moiety

Compounds of formula STR1 wherein R1 is hydrogen or one or more specified substituents, X is --O-- or --NR2 -- where R2 is lower alkyl, lower alkenyl, lower alkynyl, aryl or specified substituted lower alkyl or R2/su